Gregory received his Bachelor Degree from the IIT Institute of Design in Chicago in 1979. Creating works that blurred the distinction between painting and photography, at the age of 49 he returned to graduate school to strengthen his knowledge of art history and video-making. In 2008 he received his Master of Fine Art from Indiana University.
Gregory’s recent mixed media work combines traditional oil painting on panel with flat screen HD video and archival digital printing, creating layer upon layer of illusion with genuine wit and humour. As well as exploring (and confounding) our assumptions about the individual media of painting, photography and video, his works also comment upon the human condition: humour, play, desire, identity, loneliness and melancholy.
Gregory often includes paintings by other artists in his work, from 17th century Dutch masters to the contemporary Thomas Kinkade ‘Painter of Light’, to poignant and occasionally ironic effect.